Acetone → t-Butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-amidinobenzoyl)ureido]phenyl]propionate, acetate salt

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Reaction Steps

In a similar manner to Example 1, t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-thiocarbamoylbenzoyl)ureido]phenyl]propionate (2.4 g) was reacted with iodomethane (20 ml) and acetone (150 ml) and the resultant product was treated with ammonium acetate (4.4 g), methanol (50 ml) and dichloromethane (50 ml) at ambient temperature. This yielded a crude pale yellow solid (2.3 g), which was crystallised from hot isopropanol to give the title compound (1.35 g) as an off-white solid: NMR Spectrum (DMSO-d6) 0.81 (3H, t), 1.06 (1.2H, d), 1.24 (2H, m), 1.39 (11H, m), 1.78 (3H, s), 2.71 (2H, m), 2.82 (1H, m), 2.98 (1H, m), 3.81 (0.2H, m), 3.99 (1H, m), 7.18 (2H, d), 7.54 (2H, d), 7.94 (2H, d), 8.15 (2H, d), 8.50-10.50 (2H, br), 10.87 (1H, br s); Mass Spectrum m/Z 546 (M+H)+ ; Elemental Analysis: calculated for C26H35N5O6S. 1.0 CH3CO2H. 0.5 H2O 0.2 (CH3)2CHOH: C, 54.8%; H, 6.69%; N, 11.2%; found: C, 54.8%; H, 6.8%; N, 11.0%.

Provenance & Evidence